KR100741406B1 - Edible plant oil which were removed saturated fatty acid therefrom and chemical process thereof - Google Patents

Abstract

A method of manufacturing edible oil in which saturated fatty acid is removed by subjecting edible vegetable oil to chemical treatment to remove saturated fatty acid and reconstituting with unsaturated fatty acid is provided. The edible oil contains useful components for the body and is beneficial to human body. First, edible vegetable oil is trans-esterified with C1-8 alkanol in the presence of C1-8 alkoxide catalyst of alkali or alkaline earth metals, neutralized with organic acid or inorganic acid and removed in the alkanol to produce an alkyl ester mixture of saturated and unsaturated fatty acid. Second, the alkyl ester mixture of saturated and unsaturated fatty acid is reacted with urea dissolved in C1-8 alkanol to remove a complex of fatty acid alkyl ester and urea. Then 3mol of the separated unsaturated fatty acid alkyl ester is mixed with triglyceride comprising C1-8 low molecular weight fatty acid and trans-esterified with C1-8 alkanol in the presence of C1-8 alkoxide catalyst of alkali or alkaline earth metals. The vegetable oil is selected from corn oil, bean oil rape seed oil, grape seed oil, linseed oil, sesame oil, olive oil, perilla oil, walnut oil, pine-nut oil, peanut oil, sunflower oil, safflower oil, cotton seed oil, palm oil, red pepper oil, rice bran oil, pumpkin seed oil, green tea oil, Almond oil, evening primrose oil and hazelnut oil.

Description

Technical Field The present invention relates to an edible oil having a saturated fatty acid and a method for producing the edible oil,

The present invention relates to vegetable cooking oil from which saturated fatty acids have been removed and a method for producing the same. Vegetable oil used for edible purposes contains a large amount of unsaturated fatty acids and is currently used for food without special processing. However, since oil of warm-blooded animal having a high saturated fatty acid content is dangerous to cause various circulatory diseases, it is almost used for edible oil or food processing none. However, there is a large amount of saturated fatty acids contained in various meat and meat-processed foods that are frequently consumed in the daily diet, and in the case of various vegetable foods, one of the stocks, oil containing a considerably large amount of saturated fatty acids There are many cases in which excessive amounts of saturated fatty acids are ingested unless special attention is paid to the daily diet. Especially, in middle-aged poultry with many opportunities for eating out, there is a high possibility of consuming saturated fatty acid because of the possibility of eating meat. Therefore, it is difficult for most people to escape fear of diseases of various circulatory system after adulthood.

Polyunsaturated fatty acids (PUFAs) in foods have a role in lowering serum lipids and serum cholesterol levels, while saturated fatty acids elevate these indicators. The elevated activity of saturated fatty acids is a decrease in polyunsaturated fatty acids It is necessary to establish and prepare a method for producing edible oil from which saturated fatty acid has been removed from vegetable cooking oil

Saturated fatty acids and unsaturated fatty acids in vegetable oils are randomly distributed in triglyceride molecules, so saturated and unsaturated fatty acids are mostly bound to the same triglyceride molecule. Therefore, only the saturated fatty acid can not be completely removed by the physical method of removing the triglyceride of the saturated fatty acid by the low-temperature crystallization method generally used in the maintenance industry at present. In fact, the content of saturated fatty acids in vegetable cooking oil is relatively low (in most cases 33% or less) and it is difficult for triglycerides composed of only saturated fatty acids to exist. Therefore, it is impossible to completely remove only saturated fatty acids in the cooking oil by low temperature crystallization. Tropical vegetable oils such as palm oil or coconut palm oil with a saturated fatty acid content of more than 50% contain a significant amount of triglycerides composed only of saturated fatty acids, so that the low-temperature crystallization method can remove the triglycerides of saturated fatty acids to a considerable level, It is impossible to completely remove even the saturated fatty acid in the mixed triglyceride in which the fatty acid and the unsaturated fatty acid are bonded together in the same triglyceride molecule. In order to completely remove saturated fatty acids from vegetable cooking oil, the present inventors have established a simple and economical new method by combining the following three known organic reactions.

That is, 1) treating edible oil by a transesterification reaction so that a saturated fatty acid and an unsaturated fatty acid are not bound in the same molecule to obtain an alkyl-ester mixture of a saturated fatty acid and an unsaturated fatty acid, 2) forming a crystalline molecular complex of the alkyl-ester of saturated fatty acid and urea to obtain an alkyl ester mixture of a fatty acid consisting solely of unsaturated fatty acids; and 3) converting the unsaturated fatty acid-alkyl ester into triacetin triacetin, and glycerine-triacetate to reconstitute triglycerides by the interesterification method, thereby establishing a very simple and economical method for producing edible oils from which saturated fatty acids have been removed. This is very industrially practical I think. In the present invention, the prior art for the reaction of the interesterification reaction, which is used as a key reaction for synthesizing triglyceride, was investigated. As a result, it was found that the triglyceride having the longest carbon number and the shortest fatty acid were mixed, (Publication No. 05434278 US) in which the properties of fat are changed by randomization of fatty acid distribution among the triglycerides through the Shaun reaction, but the alkyl-ester and triacetin in the unsaturated fatty acid are interesterified There was no example in which triglyceride was synthesized by the reaction and there was no example in which these three kinds of known organic reactions were assembled for the purpose of producing edible oil from which only saturated fatty acid was removed starting from edible oil as in the present invention.

The Sigma-Aldrich catalog contains a mixture of 50-50 ratios of triolein and trinolane, but this does not indicate the retention time of various triglycerides in the high-performance liquid chromatography (HPLC) It is made by mixing 50% of purely synthesized glycerin-triolate and glycerin-trinolate for the purpose of use as a reference standard. It is not made by removing only saturated fatty acid from edible oil.

The present inventors have already performed the saponification of linseed oil to remove saturated fatty acids while destroying the toxic components cyanogen-glycosides and cyclic-nona peptides in linseed oil, Then, a saturated fatty acid is removed by a fatty acid-urea-molecular complex method to obtain an unsaturated fatty acid mixture, and then a method of making triglyceride through a fatty acid acid chloride is established and registered as a patent (Korean Patent Registration No. 10-0663063) .

However, in case of general cooking oil, it is not necessary to remove toxic components, so it is necessary to establish a simpler and more economical method. The difference from the method that I used in patent for the method of removing saturated fatty acid in edible oil is that I used 1) Transesterification reaction instead of the saponification reaction, 2) elimination of alkyl esters of saturated fatty acids by fatty acid-alkyl ester-urea complex method instead of fatty acid-urea complex, and 3) synthesis of triglycerides via acid chloride of unsaturated fatty acids Instead of the synthetic method, the entire process of making edible oil starting from vegetable oil and completely eliminating saturated fatty acid by reconstituting triglyceride by an esteresterification reaction with unsaturated fatty acid-alkyl ester with triacetin is a very economical and easy new It is a way of establishing the method. Vegetable oil is consumed too much and its price is so cheap that the process of eliminating saturated fatty acids is very complicated, or if the processing cost is too high, it is difficult to use it realistically. In this process, a large amount of expensive anhydrous alkanol is used in the transesterpicase reaction, and the alkoxide of the alkali or alkaline earth metal used as the catalyst is destroyed after the reaction Unlike the conventional method using mineral acid which is diluted with water, by using glacial acetic acid, it is possible to recover 100% of anhydrous alkanol and to recycle it for the same purpose, so that it can be used for transesterification reaction And the amount of the anhydrous alkanol was significantly reduced.

In addition, the edible oil directly stimulates our taste, and the flavor of the final product, which is processed, significantly differs from the flavor of the starting oil, vegetable oil. In addition, chemical residues should not be left in the chemical process due to changes in the chemical nature of the oil components or due to the reagents used.

The three organic chemistries, which are the core of this new technology, use only reactions that do not cause any change in unsaturated fatty acids, such as oxidation or reduction, other than those that disassemble ester bonds in oil and then reconstitute. Alkoxide, alkoxide, alkaline or alkaline earth metal alkoxide, urea, and triacetin can not only be completely removed after the reaction is completed, but also can be used safely in food processing as defined by the World Health Organization the so-called GLAS -list are included in the (G enerally R ecognized a s S afe for Food) that the organic reactions of these three species are not to be a problem is used in the processing of fatty foods.

The present invention provides a method for producing vegetable cooking oil which is obtained by chemical treatment of vegetable cooking oil in the following step a) -c) to remove saturated fatty acid and reconstituted with only unsaturated fatty acid.

a) vegetable cooking oil is subjected to a polycation reaction with an alkanol having 1-8 carbon atoms in the presence of an alkoxide catalyst having 1-8 carbon atoms of an alkali or alkaline earth metal, neutralized with an organic acid or an inorganic acid, Obtaining an unsaturated fatty acid alkyl ester mixture;

b) reacting the fatty acid-alkyl ester mixture obtained in a) with urea dissolved in an alkanol having from 1 to 8 carbon atoms to precipitate an alkyl ester-urea molecular complex of saturated fatty acid by crystallization;

c) mixing 3 moles of the alkyl ester of the unsaturated fatty acid separated in b) with triglyceride consisting of a low molecular weight fatty acid having 1 to 8 carbon atoms and subjecting the ester to a polycation reaction in the presence of an alkoxide catalyst of an alkali or a potassium metal To obtain a vegetable cooking oil composed of only the unsaturated fatty acid which is reconstituted with the triglyceride structure.

The present invention also relates to a process for removing saturated fatty acids produced by the above-

And to provide vegetable cooking oil reconstituted with an unsaturated fatty acid.

The present invention will be described in more detail,

1) the process of making an alkyl-ester of a fatty acid by treating edible oil with a transesterification reaction,

2) Alkali or alkaline earth metals used in the transesterification process. Alkoxides of 1-8 carbon atoms used in this process by destroying the alkoxide by adding an equivalent amount of organic acid or inorganic acid to the alkoxide of 1-8 carbon atoms The process of recovering the alkanol and making it economical by recycling it next time,

3) a process of removing an alkyl-ester of a saturated fatty acid by a urea-complex method and

4) The alkyl ester of the unsaturated fatty acid is mixed with triglyceride of a fatty acid having 1 to 8 carbon atoms and an alkoxide having a catalytic amount of alkaline or an alkaline earth metal of 1-8 carbon atoms, and interesterification of the triglyceride with the unsaturated fatty acid alone.

In order to investigate the reaction conditions of the interesterification reaction, which is the final step of the reaction of these four steps, a mixture of triacetin and ethyl-palmitate was subjected to an interesterification ) Reaction was carried out in the same manner as in Example 1, and the chemical structure of the reaction product was analyzed by spectrometry. As a result, monoglyceride, diglyceride, And triglycerides were synthesized smoothly. Therefore, we conducted a synthesis experiment of vegetable oil with saturated fatty acid removed from various vegetable oil, and obtained satisfactory results in the yield analysis and fatty acid composition analysis experiment for the final product as follows there was. In order to carry out the experiment to make edible oil with saturated fatty acid by the method as described above for the commercially available edible oil, the following 22 kinds of vegetable edible oil which can be obtained in the domestic market were tested, The edible oil used in the experiment was as follows.

1) corn oil 2) soybean oil 3) rapeseed oil 4) grape seed oil 5) linseed oil 6) sesame oil 7) olive oil 8) perilla oil 9) ) Sunflower oil, safflower oil, 14) cottonseed oil, 15) palm oil, 16) red pepper seed oil, 17) rice bran oil, 18) pumpkin seed oil, Seed oil, 20) almond oil, 21) evening primrose oil, and 22) hazelnut oil.

The lower alkanol used in the present invention means a lower alcohol having 1 to 8 carbon atoms and means methanol, ethanol, propanol, isobutanol, pentanol, hexanol, heptanol and octanol.

In the alkoxide of 1 to 8 carbon atoms of the alkali or alkaline earth metal used in the present invention, the alkali and alkaline earth metals mean lithium, sodium, potassium, magnesium and calcium. Examples of triglycerides composed of low molecular weight fatty acids that can be used in the present invention include glycerol-triformate, triacetin, glycerol-triacetate, glycerol-tripropionate, glycerol- Tributyrin (glycerol-tributyrate),

Glycerol-tricaprylate, glycerol-triheptanoate, glycerol-triheptanoate, glycerol-tricaprylate, and glycerol- ≪ / RTI > can be used.

As the organic acid or inorganic acid used in the present invention, an acid selected from hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, propionic acid or butyric acid may be used. Among them, it is preferable to use formic acid and acetic acid. Particularly, it is most preferable to use glacial acetic acid.

Hereinafter, the present invention will be described in more detail by way of examples.

Example 1

Manufacture of edible oil from which saturated fatty acids in corn oil have been removed:

50.29 gm of dehydrated corn oil was decompressed in a silicone-oil bath heated to 105 ° C for about 30 minutes, mixed with 250 ml of anhydrous ethanol, and 250 μl of sodium-methoxide (28% Followed by stirring with a magnetic stirrer for about 5 hours, the transesterpicase reaction proceeds and the interface between the oil layer and the ethanol layer disappears and becomes a transparent solution. To stop the reaction, a solution of 70 g of equivalent amount of glacial acetic acid was added to neutralize sodium methoxide, 80 gm of urea was dissolved in 250 ml of anhydrous ethanol, and the mixture was kept warm. Upon cooling and standing overnight, the ethyl ester of the saturated fatty acid forms a urea complex and precipitates as crystals. The crystals were removed by suction filtration and the filtrate was concentrated under reduced pressure to recover the anhydrous ethanol. After concentration, a small amount of water and d-HCl were added to the residue to destroy the urea-complex of the unsaturated fatty acid to precipitate the unsaturated fatty acid Then, extraction with hexane and concentration of hexane yields 43 gm of the ethyl ester of the unsaturated fatty acid. When GLC analysis is performed on the unsaturated fatty acid obtained by removing the saturated fatty acid by the urea-complex method and by making the ethyl ester by the transesterpicase reaction of the corn oil, before the removal of the saturated fatty acid ; Saturated fatty acids; 14.80%, oleic acid; 33.30%, linoleic acid; 48.10% linolenic acid; It has a fatty acid composition of 0.80%. After removal of saturated fatty acids ; Saturated fatty acids; 0.00%, oleic acid; 22.30%, linoleic acid; 76.43%, linolenic acid; 1.27%. The urea - complex method showed that the fatty acid composition before and after the removal of ethyl ester of saturated fatty acid showed that most of the saturated fatty acid was removed and part of oleic acid was removed from the unsaturated fatty acids, , While that of unleavened linoleic acid increased from 48.1% to 76.43%, while that of untreated rice decreased from 33.3% to 22.30%. After 43 gm of the ethyl ester of the unsaturated fatty acid was dried well, 10.55 gm of glycerine-triacetate and 250 μl of 28% -sodium methoxide solution were mixed and then the triglyceride of the unsaturated fatty acid When the pressure is reduced to 50 mm / Hg or less while heating at 90 to 125 ° C in a silicone oil bath to re-synthesize the seride, the esterase reaction proceeds and ethyl acetate is removed and triglyceride composed of unsaturated fatty acid alone . When the reaction is completed and there is no further bubbling, the weight loss due to bubbling is 10.7 gm. The reaction mixture is neutralized by adding 70 μl of glacial acetic acid, water is added, and the mixture is repeatedly extracted with hexane. When the mixture is concentrated, the saturated fatty acid is removed and 32.6 gm of edible oil (triglyceride type) composed of only unsaturated fatty acids is obtained.

Example 2

Manufacture of edible oil from which saturated fatty acids in soybean oil have been removed:

When 50.34 gm of soybean oil thoroughly dehydrated by decompressing in a silicone oil bath heated to 105 캜 for about 30 minutes was treated in the same manner as in Example 1 , most of the saturated fatty acids and some of the oleic acid were removed and the soybean oil (triglyceride 31,34 gm is obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids ; Saturated fatty acids; 14.70%, oleic acid; 23.0%, linoleic acid; 45.20%, linolenic acid; 6.5%, after removal of saturated fatty acids ; Saturated fatty acids; 0,00%, oleic acid; 20.73%, linoleic acid; 51.70% linolenic acid; 8.21%.

Example 3

Seed oil  Preparation of edible oil with saturated fatty acid removed:

50.91 gm of the dehydrated soybean oil thoroughly dehydrated in a silicone oil bath heated to 105 캜 for about 30 minutes was treated in the same manner as in Example 1 to remove most of the saturated fatty acid and partially oleic acid, 42.63 gm is obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids ; Saturated fatty acids; 6.8%, oleic acid; 49.56%, linoleic acid; 24.10% linolenic acid; 9.20%, after removal of saturated fatty acids ; Saturated fatty acids; 0.00%, oleic acid; 53.74%, linoleic acid; 28.74% linolenic acid; 11.25%.

Example 4

Preparation of edible oil from which saturated fatty acids in grape seed oil are removed:

When 50.21 gm of grape seed oil dehydrated thoroughly by decompressing for about 30 minutes while heating at 105 캜 was treated in the same manner as in Example 1 , the whole of saturated fatty acid and some oleic acid were removed, and grape seed oil 38.04 gm reconstituted with unsaturated fatty acid alone . The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 10.08%, oleic acid; 18.40%, linoleic acid; 68.80%, after removal of saturated fatty acids; Saturated fatty acids; 0%, oleic acid; 12.01%, linoleic acid; 87.99%.

Example 5

Linseed oil  Preparation of edible oil with saturated fatty acid removed:

49.86 gm of dehydrated linseed oil was decompressed for about 30 minutes while heating at 105 DEG C and treated in the same manner as in Example 1. The amount of sodium methoxide used and the amount of glacial acetic acid used in the transesterification process and the interesterification process Were changed to 320 μl and 90 μl, respectively. When the experiment was conducted, most of the saturated fatty acids were removed and 42.13 gm of flaxseed oil reconstituted with unsaturated fatty acids alone was obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 9.4%, oleic acid; 21.1%, linoleic acid; 15.0%, linolenic acid; 52.4%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 11,79%, linoleic acid; 16.67%. Linolenic acid; 69,74%

Example 6

Preparation of cooking oil with saturated fatty acid removed from sesame oil:

50.71 gm of dehydrated sesame oil was decompressed for about 30 minutes while being heated to 105 캜 and treated in the same manner as in Example 1. The amounts of sodium methoxide and glacial acetic acid were measured in the transesterification process and the interesterification process 850 μl and 240 μl, respectively. When the experiment was conducted, most of the saturated fatty acids were removed and the reconstituted sesame oil 38.10 gm was obtained with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Saturated fatty acid Before removal; Saturated fatty acids; 15.20%, oleic acid; 38.30%, linoleic acid; 45.40%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 44.13%, linoleic acid; 55.87%.

Example 7

Preparation of Edible Oil from Olive Oil with Saturated Fatty Acid:

50.09 gm of dehydrated olive oil was decompressed for about 30 minutes while being heated to 105 DEG C and treated in the same manner as in Example 1. The amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process was 350 μl, and 100 μl, the majority of the saturated fatty acids were removed, resulting in 29.60 gm of olive oil reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Saturated fatty acid Before removal; Saturated fatty acids; 12.50%, oleic acid; 74.10%, linoleic acid; 3.80%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 87.04%, linoleic acid; 10.10%.

Example 8

Manufacture of edible oil with saturated fatty acid removed from perilla oil:

The mixture was decompressed for about 30 minutes while being heated to about < RTI ID = 0.0 > 05 C < / RTI > to obtain thoroughly dehydrated perilla oil 50.33 gm and treated in the same manner as in Example 1 except that the sodium methoxide and glacial acetic acid usage in the transesterification process and interesterification process Were changed to 400 μl and 110 μl, respectively. When the experiment was conducted, most of the saturated fatty acid was removed and the reconstituted perilla oil was obtained with the unsaturated fatty acid alone of 41.35 gm. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Saturated fatty acid Before removal; Saturated fatty acids; 8.70%, oleic acid; 16.38%, linoleic acid; 16.60% linolenic acid; 58.32% after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 12.61%, linoleic acid; 19.34%. Linolenic acid; 66.30%

Example 9

From Hodo Oil  Production method of edible oil from which saturated fatty acid is removed:

After heating to 150 ° C, decompression was carried out for about 30 minutes to obtain 50.06 gm of horseradish oil, which was thoroughly dehydrated and treated in the same manner as in Example 8 to obtain 29.86 gm of horseshoe oil reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Saturated fatty acid Before removal; Saturated fatty acids; 7.90%, oleic acid; 22.40%, linoleic acid; 58.30% linolenic acid; 8.10%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 17.84%, linoleic acid; 70.83%. Linolenic acid; 10.28%.

Example 10

Preparation of edible oil from which saturated fatty acid was removed from pine nuts:

1 50.04 gm of the dehydrated noodle oil was thoroughly decompressed for about 30 minutes while being heated to 05 ° C and treated in the same manner as in Example 1 except that sodium methoxide and glacial acetic acid were used in the transesterification process and the interesterification process When 300 μl and 80 μl were added, the most of the saturated fatty acid was removed and the reconstituted noodle oil was obtained with 39.28 gm. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Saturated fatty acid Before removal; Saturated fatty acids; 7,40%, oleic acid; 27.30%, linoleic acid; 45.20%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 27.52%, linoleic acid; 50.43%.

Example 11

From peanut oil  Manufacture of edible oil from saturated fatty acids:

50.29 gm of deep-rooted dehydrated ground oil was decompressed for about 30 minutes while being heated to 105 캜, and treated in the same manner as in Example 1, except that the amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process When the experiment was carried out with different portions increased by 400 μl and 110 μl, most of the saturated fatty acids were removed and 27.22 gm of peanut oil reconstituted with only unsaturated fatty acid was obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 13.70%, oleic acid; 43.10%, linoleic acid; 35.40%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 51.60%, linoleic acid; 48.40%.

Example 12

Manufacture of Edible Oil from Saturated Fatty Acid from Sunflower Oil:

50.17 gm of deep-rooted dehydrated ground oil was decompressed for about 30 minutes while being heated to 105 캜 and treated in the same manner as in Example 1, except that the amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process was When the experiment was conducted with different portions increased by 500 μl and 140 μl, most of the saturated fatty acids were removed and 35.19 gm of sunflower oil reconstituted with unsaturated fatty acids alone was obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 11.40%, oleic acid; 19.70%, linoleic acid; 66.60%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 22.00%, linoleic acid; 74.40%.

Example 13

In safflower oil  Manufacture of edible oil from saturated fatty acids:

50.18 gm of dehydrated safflower was thoroughly decompressed for about 30 minutes while being heated to 105 DEG C and treated in the same manner as in Example 1. The amounts of sodium methoxide and glacial acetic acid were measured in the transesterification process and the interesterification process 600 μl, and 170 μl, the majority of the saturated fatty acids were removed, resulting in 28.50 gm of safflower oil reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 8.60%, oleic acid; 11.90%, linoleic acid; 79.50%, after removing saturated fatty acid; Saturated fatty acids; 0.00%, oleic acid; 10.48%, linoleic acid; 85.82%.

Example 14

Preparation of edible oil from which saturated fatty acid is removed from cottonseed oil:

50.01 gm of cottonseed oil thoroughly dehydrated by heating at 105 DEG C for about 30 minutes was treated in the same manner as in Example 1 while the amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process was 200 μl, and 50 μl, the majority of the saturated fatty acids were removed, resulting in 25.11 gm of cottonseed oil reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 21.80%, oleic acid; 14.50%, linoleic acid; 46.100%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 15.71%, linoleic acid; 84.29%.

Example 15

Manufacture of edible oil with saturated fatty acid removed from palm oil:

51.01 gm of palm oil sufficiently dried at 105 ° C was treated in the same manner as in Example 1 except that the amounts of sodium methoxide and glacial acetic acid used were increased to 850 μl and 200 μl respectively in the transesterification process and the amount of urea used was changed to 260 gm The saturated fatty acid was completely removed. At this time, only 3.4 gm of the ethyl ester of the unsaturated fatty acid was obtained. In the case of the esterification reaction in the same manner as in the other examples, the final edible oil having the saturated fatty acid removed was 2.91 gm is obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 45.40%, oleic acid; 39.30%, linoleic acid; 10.40%, linolenic acid; 0.00%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 33.12%, linoleic acid; 66.88%. Linolenic acid; 0.00%.

Example 16

From red pepper seed oil  Manufacture of edible oil from saturated fatty acids:

50.03 gm of dehydrated red pepper seed oil, which was decompressed for about 30 minutes while being heated to 105 캜, was treated in the same manner as in Example 1, and the amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process When the experiment was carried out with different portions increased by 400 μl and 110 μl, most of the saturated fatty acids were removed and 28.56 gm of red pepper seed oil reconstituted with only unsaturated fatty acids was obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 19.37%, oleic acid; 18.68%, linoleic acid; 57.54%, linolenic acid; 4.41%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 10.34%, linoleic acid; 81.41%. Linolenic acid; 8.25%

Example 17

From rice bran oil  Manufacture of edible oil from saturated fatty acids:

50.28 gm of rice bran oil which had been thoroughly dehydrated by heating at 105 DEG C for about 30 minutes was treated in the same manner as in Example 1. The amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process was 400 μl, and 110 μl, the majority of the saturated fatty acid was removed, resulting in 29.26 gm of rice bran oil reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 16.90%, oleic acid; 42.70%, linoleic acid; 39.30% linolenic acid; 1.10%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 32.54%, linoleic acid; 64.31%. Linolenic acid; 3.15%

Example 18

From pumpkin seed oil  Manufacture of edible oil from saturated fatty acids:

50.96 gm of pumpkin seed oil which had been thoroughly dehydrated by heating at 105 ° C for about 30 minutes was treated in the same manner as in Example 1 except that the amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process When the experiment was carried out with different portions increased by 300 μl and 80 μl, most of the saturated fatty acids were removed and 36.67 gm of pumpkin seed oil reconstituted with only unsaturated fatty acids was obtained. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 9.00%, oleic acid; 34.34%, linoleic acid; 49.27% linolenic acid; 7.39%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 28.04%, linoleic acid; 61.05%. Linolenic acid; 10.91%

Example 19

From green tea seed oil  Manufacture of edible oil from saturated fatty acids:

50.35 gm of dehydrated green tea seed oil was decompressed for about 30 minutes while being heated to 105 캜 and treated in the same manner as in Example 1 except that the amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process Were changed to 400 μl and 110 μl, respectively. When the experiment was conducted, most of the saturated fatty acids were removed and the reconstituted green tea seed oil was obtained with only 28.68 gm of unsaturated fatty acid. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 16.50%, oleic acid; 57.07%, linoleic acid; 24.26% linolenic acid; 2.17%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 48.36%, linoleic acid; 48.52%. Linolenic acid; 3.12%

Example 20

Manufacture of edible oil from which saturated fatty acids have been removed from almond oil:

50.75 gm of almond oil which had been thoroughly dehydrated by heating at 105 DEG C for about 30 minutes was treated in the same manner as in Example 1 except that the amount of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process Experiments were conducted with different amounts of 200 μl and 50 μl, respectively, and the majority of the saturated fatty acids were removed, resulting in 41.78 gm of almond oil reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 5.34%, oleic acid; 77.92%, linoleic acid; 16.74%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 73.75%, linoleic acid; 26.25%.

Example 21

Preparation of edible oil from which saturated fatty acids are removed from evening primrose oil:

50.23 gm of dehydrated evening primrose oil was decompressed for about 30 minutes while being heated to 105 캜 and treated in the same manner as in Example 1 except that sodium methoxide and glacial acetic acid were used in the transesterification process and the interesterification process When the experiment was carried out with different portions increased by 300 μl and 80 μl, most of the saturated fatty acids were removed and 42.34 gm of the evening primrose oil was reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 6.14%, oleic acid; 8.86%, linoleic acid; 73.50%, linolenic acid; 11.50%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 5,31%, linoleic acid; 78.26% linolenic acid; 16.43%.

Example 22

Hazelnut  Production of edible oil from which saturated fatty acid has been removed from oil:

50.48 gm of dehydrated and dehydrated soybean oil was decompressed for about 30 minutes while being heated to 105 캜 and treated in the same manner as in Example 1 except that the amounts of sodium methoxide and glacial acetic acid used in the transesterification process and the interesterification process Was changed to 5400 μl and 110 μl, respectively. When the experiment was conducted, most of the saturated fatty acids were removed, resulting in 32.14 gm of hazelnut oil reconstituted with only unsaturated fatty acids. The composition of fatty acids before and after the removal of saturated fatty acids is as follows. Before the removal of saturated fatty acids; Saturated fatty acids; 12.60%, oleic acid; 71.48%, linoleic acid; 15.42%, linolenic acid; 0.50%, after removal of saturated fatty acids; Saturated fatty acids; 0.00%, oleic acid; 64.56%, linoleic acid; 34.23%, linolenic acid; 1.21%

All edible oils were treated in the same manner as above, but the amount of urea used was adjusted according to the content of saturated fatty acid.

Experimental Example 1

Fatty acid analysis of various edible oils obtained in the above Examples was carried out by the following method.

Dissolve 20 μl of the vegetable oil sample in 100 μl of 28% sodium methoxide, add 100 μl of hexane, mix well and centrifuge. 5 μl of the supernatant is diluted with 95 μl of hexane, And injected into a chromatographic analyzer. When analyzing the ethyl esters of fatty acids, 10 μl of fatty acid ester was diluted with 2 ml of hexane, then diluted 10 times with hexane, and 5 μl of the diluted fatty acid ester was injected into a GLC analyzer. Analytical instrument: Hewlett packard 5890 Ⅱ series (HP Co., Wilmington, DE, USA), detector; FID, Column: DB-23 (60m * 0.25mm ID, 0.25m) Oven temperature: initial 130 ° C, final 230 ° C, increasement: 2.7 ° C / min, inlet temp: 270 ° C, detector temp: nitrogen, flow rate: 30 ml / min

The GLC analysis (%, w / w) for the fatty acid composition before saturated fatty acid digestion and after saturated fatty acid digestion is shown in Table 1 below.

Table 1. GLC analysis (%, w / w) on fatty acid composition before and after removal of saturated fatty acids for various edible oils ; The saturated fatty acid content is the sum of the stearin content and the palmitic acid content only.

The vegetable oil in which the saturated fatty acid produced by the method of the present invention is removed is very useful for the human body as the edible oil since the saturated fatty acid is completely removed and the triglyceride composed only of the unsaturated fatty acid is obtained.

Claims (6)

A method for producing vegetable cooking oil by removing the saturated fatty acid by chemical treatment of the vegetable cooking oil in the following step a) -c) and reconstituting the vegetable cooking oil by using only the unsaturated fatty acid a) A method for producing a vegetable cooking oil by adding vegetable cooking oil to an alkoxide having 1-8 carbon atoms of an alkali or alkaline earth metal Reacting an alkanol having 1 to 8 carbon atoms with a transesterpicase in the presence of a catalyst, neutralizing with an organic acid or an inorganic acid, and removing the alkanol to obtain a saturated and unsaturated fatty acid alkyl ester mixture; b) reacting the fatty acid-alkyl ester mixture obtained in a) with urea dissolved in an alkanol having from 1 to 8 carbon atoms to precipitate an alkyl ester-urea molecular complex of saturated fatty acid by crystallization; c) mixing 3 moles of the alkyl ester of the unsaturated fatty acid separated in b) with triglyceride consisting of a low molecular weight fatty acid having 1 to 8 carbon atoms and reacting with an ester of an ester of an alkali or alkaline earth metal in the presence of an alkoxide catalyst having 1-8 carbon atoms The step of obtaining the vegetable cooking oil consisting of only the unsaturated fatty acid having the triglyceride structure reconstituted after the completion of the lipification reaction is separated. The vegetable oil according to claim 1, wherein the vegetable oil is selected from the group consisting of corn oil, soybean oil, rapeseed oil, grape seed oil, flaxseed oil, sesame oil, olive oil, perilla oil, walnut oil, pine oil, peanut oil, sunflower oil, safflower oil, cottonseed oil, , Pumpkin seed oil, green tea seed oil, almond oil, evening primrose oil, and hazelnut oil. The method according to any one of claims 1 to 4, wherein the alkoxide of the alkali or alkaline earth metal is selected from the group consisting of lithium, sodium, potassium, magnesium or alkoxides of calcium. The method according to claim 1, wherein an acid selected from hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, propionic acid or butyric acid is used as the organic acid or inorganic acid. In paragraph 1 (c), glycerol-triphorate as a triglyceride composed of a low molecular weight fatty acid, Glycerol-triacetate, Tripropionin (glycerol-tripropionate), Glycerol-tributyrate, Trivalerin (glycerol-trivalerate), < RTI ID = 0.0 > Tricaproin (glycerol-tricaproate), Triheptanoin (glycerol-triheptanoate) and Wherein one triglyceride selected from tricaprylin (glycerol-tricaprylate) is used. A vegetable oil edible oil which is prepared by one of the methods selected in claims 1 to 5 and which is obtained by removing saturated fatty acids and reconstituted with unsaturated fatty acids alone.